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Komeyama K, Itai Y, Takaki K. Practical Stannylation of Allyl Acetates Catalyzed by Nickel with Bu3 SnOMe. Chemistry. 2016;22(27):9130-4doi: 10.1002/chem.201601515.
Komeyama, K., Itai, Y., & Takaki, K. (2016). Practical Stannylation of Allyl Acetates Catalyzed by Nickel with Bu3 SnOMe. Chemistry (Weinheim an der Bergstrasse, Germany), 22(27), 9130-4. https://doi.org/10.1002/chem.201601515
Komeyama, Kimihiro, et al. "Practical Stannylation of Allyl Acetates Catalyzed by Nickel with Bu3 SnOMe." Chemistry (Weinheim an der Bergstrasse, Germany) vol. 22,27 (2016): 9130-4. doi: https://doi.org/10.1002/chem.201601515
Komeyama K, Itai Y, Takaki K. Practical Stannylation of Allyl Acetates Catalyzed by Nickel with Bu3 SnOMe. Chemistry. 2016 Jun 27;22(27):9130-4. doi: 10.1002/chem.201601515. Epub 2016 May 25. PMID: 27124370.
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Chemistry. 2016 Jun 27;22(27):9130-4. doi: 10.1002/chem.201601515. Epub 2016 May 25.

Practical Stannylation of Allyl Acetates Catalyzed by Nickel with Bu3 SnOMe.

Chemistry (Weinheim an der Bergstrasse, Germany)

Kimihiro Komeyama, Yuuhei Itai, Ken Takaki

Affiliations

  1. Department of Applied Chemistry, Graduate School of Engineering, Hiroshima University, 1-4-1 Kagamiyama, Higashi, Hiroshima, 739-8527, Japan. [email protected].
  2. Department of Applied Chemistry, Graduate School of Engineering, Hiroshima University, 1-4-1 Kagamiyama, Higashi, Hiroshima, 739-8527, Japan.

PMID: 27124370 DOI: 10.1002/chem.201601515

Abstract

A practical and scalable nickel-catalyzed allylic stannylation of allyl acetates with Bu3 SnOMe is described. A variety of acyclic and cyclic allyl acetates, even with base-sensitive moieties, undergoes the stannylation by using NiBr2 /4,4'-di-tert-butylbipyridine (dtbpy)/Mn catalyst system to afford highly functionalized allyl stannanes with excellent regioselectivity and yields. Furthermore, the scope of protocol is also extended by the reaction of propargyl acetates, giving rise to propargyl or allenyl stannanes. Additionally, a unique diastereoselectivity using the nickel catalyst different from the palladium was demonstrated for the stannylation of cyclic allyl acetates. In the reaction, inexpensive and stable nickel complexes, abundant reductant (Mn), and atom-economical stannyl source were used.

© 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Keywords: allyl stannanes; nickel; stannyl alkoxide; stannylation; synthetic method

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